Our invention relates to a two-step process for producing phenyl-and cyclohexyl-substituted oxybutane derivative-containing mixtures of our invention by means of first reacting methyl ethyl ketone with benzaldehyde in the presence of a sulfonic acid catalyst to produce a mixture of phenyl pentenone derivatives having the structures: ##STR1## and then hydrogenating the resulting mixture of phenyl pentenone derivatives in the presence of a hydrogenation catalyst as well as the product produced thereby which is a mixture of compounds having the structures: ##STR2## and perfumery uses thereof for augmenting, enhancing or imparting aromas in and to perfume compositions, colognes and perfumed articles.
There has been considerable work performed relating no substances which can be used to impart (modify, augment or enhance) fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product.
Long-lasting substantive intense "wet foral" muguet, rose, green, lilac and ozoney aromas with natural green, floral, muguet and rose topnotes are highly desirable in several types of perfume compositions, perfumed articles and colognes (e.g., muguet fragrances).
Perfume uses of individual phenyl-and cyclohexyl-substituted oxybutane derivative-containing mixtures of our invention are known in the prior art. Thus, Sundt, Swiss Patent 604716 (abstracted at Chem. Abstracts Volume 89:22076g) discloses the perfumery uses of the compound having The structure: ##STR3## produced from the compound having the structure: ##STR4## Meuly, et al, U.S. Pat. No. 3,666,255 of Jun. 6, 1972 discloses the perfume use, inter alia, of the compound having the structure: ##STR5## prepared according to the reaction: ##STR6## Chmielarz, et al, Chem. Abstracts Volume 83:147254h, abstract of Tluszcze, Srodki, Piorace, Kosmet., 1975, 19(3), pages 109-18 discloses the perfume use of the compound having the structure: ##STR7## in substantially pure form (98.5-99.5 pure crystalline) prepared according to the reaction: ##STR8##
Nothing in the prior art however discloses or infers the unexpected, unobvious and advantageous properties of the phenyl-and cyclohexyl-substituted oxybutane derivative-containing mixtures of our invention prepared according to the process of our invention.